Sodium hydride → HCID 86705188, compound

HRID 2401283Notes

Reaction equation

HRID 2401283 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH:6]1[CH2:10][N:9]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[C:8](=[O:21])[NH:7]1)[CH3:5].Cl[CH2:23][C:24]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1)=[O:25].C(=O)([O-])O.[Na+]>CN(C=O)C.O>[O:21]=[C:8]1[N:9]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:19])([F:18])[F:20])=[CH:15][CH:16]=2)[CH2:10][CH:6]([CH:4]([CH3:3])[CH3:5])[N:7]1[CH2:23][C:24]([NH:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:35])[F:36])[CH:28]=1)=[O:25]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 7367442-chloro-N-[3-(trifluoromethyl)phenyl]acetamideHCID 86705189HCID 86705189, compound

Product 1

HCID 86705188HCID 86705188, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 22 mg) was added to a solution of 4-(propan-2-yl)-1-[6-(trifluoromethyl)pyridin-3-yl]imidazolidin-2-one (50 mg) in DMF (1.5 mL), and the mixture was stirred at room temperature for 15 min. After 2-chloro-N-[3-(trifluoromethyl)phenyl]acetamide (52 mg) was added thereto, the resulting mixture was stirred at room temperature for 21 hr. Water and saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, followed by extraction with chloroform. The organic layer was separated out by phase separation cartridge and concentrated under reduced pressure. The residue was purified by column chromatography (NH cartridge, and silica gel cartridge, hexane/ethyl acetate) and preparative HPLC to afford the title compound (79 mg).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 21 hr
  2. extractionfollowed by extraction with chloroform
  3. customThe organic layer was separated out by phase separation cartridge
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (NH cartridge, and silica gel cartridge, hexane/ethyl acetate) and preparative HPLC

Sources & evidence

ORD record
ord-1a4bdb6ce4f442e387e5c35bbf43fcb5
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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